Grigor Dimitrov vs. Alexei Popyrin Prediction, Betting Pick, Latest US Open Odds for Monday, August 31st
Grigor Dimitrov and Alexei Popyrin meet in a US Open first round that has historically produced tight sets whenever they share a court. Dimitrov enters as the favorite after navigating qualifying, but Popyrin's serve has repeatedly forced this matchup into tiebreak territory.
Peter Alexis - August 31, 2026, 3:35 PM EDT
4 Minute ReadGrigor Dimitrov vs. Alexei Popyrin Prediction: Can Popyrin Compete as Slight Underdog in First Round?
Dimitrov and Popyrin are scheduled for a 5:15 PM ET start, with Dimitrov favored at -203 and Popyrin at +159. The preferred market avoids choosing an outright winner and instead backs Popyrin to take at least one set while also requiring at least one tiebreak at combined -140 odds.
The head-to-head makes that combination particularly appealing. Dimitrov leads the series 2-1, but all three previous meetings have included at least one tiebreak. Their first matchup in Melbourne in 2021 went 6-4, 6-7, 6-3 to Dimitrov, Popyrin won 4-6, 7-6, 6-3 in Montreal in 2024, and Dimitrov took their most recent meeting 7-6, 6-2 later that year in Shanghai.
Grigor Dimitrov vs. Alexei Popyrin Odds
- Moneyline: Borges (+165), Tien (-200)
Grigor Dimitrov vs. Alexei Popyrin Date, Time, and Where to Watch
- Date: Monday, August 31st, 2026
- Time: 5:15 PM ET
- Where to Watch: ESPN, ESPN Unlimited
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Grigor Dimitrov vs. Alexei Popyrin Prediction
That means a tiebreak has appeared in 100% of their previous matches, while Popyrin has taken at least one set in two of three. The Australian's huge first serve is the obvious reason. When he is landing enough first deliveries, Dimitrov can struggle to create consistent break opportunities and sets quickly drift toward 5-5 or 6-6.
Dimitrov has already been through qualifying this week and looked sharp. He crushed Lorenzo Giustino 6-0, 6-3 before beating Timofey Skatov 7-6, 6-4, then advanced through the final round when Otto Virtanen withdrew. Even during that clean qualifying run, however, Dimitrov still needed a tiebreak against Skatov, fitting the same type of scoreline that Popyrin is capable of producing.
Popyrin does not need to win the match for this wager. He only needs one strong serving set, and history suggests that is realistic. He has already beaten Dimitrov outright on a hard court, and two of the three meetings required three sets even though they were played in best-of-three tournaments.
Dimitrov's return game and greater variety should eventually give him an advantage over a full five-set match, but that actually makes the combination more attractive. Popyrin can use his serve to steal one set and force another into a breaker without having to sustain his highest level for three hours.
Grigor Dimitrov vs. Alexei Popyrin Best Bet
- Best Bet: Alexei Popyrin to Win a Set + At Least One Tiebreak (-140) Check out the best odds at DraftKings Sportsbook
Three meetings, three tiebreaks and two instances of Popyrin taking a set provide unusually strong matchup evidence. The market only asks those two trends to occur in the same Grand Slam match.
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